Dessa hits a career milestone with grand Orchestra Hall performance

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“I want to try, I want to risk,” Dessa raps on her blistering takedown of Midwestern modesty, “Fighting Fish.” That line could have just as easily been the tagline for her gargantuan collaboration with the Minnesota Orchestra, which debuted Friday night and will be reprised on Saturday. Dessa herself described the production as her most ambitious gig yet, and that word, ambitious, might be the most fitting adjective to contain the wide-ranging presentation of lavish orchestral arrangements, disarming stage banter, soul-baring singing, and monologuing that sent up the TED Talk format while offering an entirely original take on dissecting heartbreak.

But the thing about describing a performance as ambitious is that it puts the emphasis on the intent and implies that the artist’s sheer audacity is more impressive than the resulting work. And the thing about Dessa’s show is that she extended the ladder up to its tallest rung, told us she was pretty nervous about how high up it was, and then scaled it as we all watched in awe.

Yes, she was trying a lot of big ideas all at once — debuting new material, experimenting with a multi-disciplinary format, collaborating with a Grammy-winning freaking orchestra — but they all worked, each as individual elements and collectively as one cohesive artistic statement. Every detail, from the sequencing of the set list, to the mesmerizing light show, to the giant bedazzled model of a piece of Dessa’s own brain (we’ll get there), to the swells of the orchestra at just the right moments, it all swirled together to paint a vivid portrait of what it means to love and lose, and what a hyper-intellectual, whiskey-drinking poet with a hopeless romantic streak and a curiosity about neuroscience must do in order to reclaim her own emotional agency and find some peace.

I’d be lying if I said I didn’t spend half the show with a knot in the back of my throat.

The evening began like a typical Minnesota Orchestra performance, with the musicians taking their seats and beginning to tune as the house lights dimmed. But the lead instrument this evening would not have a bow or a reed; as the players assumed their positions, a man dressed in all black carefully placed a single microphone in a stand at center stage. It was the kind of cordless mic I’d seen Dessa handle at venues large and small, from dimly lit dive bars to the Mainroom, but positioned alone in front of the entire orchestra and sold-out crowd it felt downright monumental. Despite the dozens of people of stage, the spotlight was going to be oriented on a one-woman show.

Suddenly that woman appeared, wearing motorcycle gloves, combat boots, and a satin jacket, suited up for her biggest battle yet. Without saying a word, she launched right into the opening song, “The Crow,” as familiar a Dessa song as there is, though it was being inverted before our very eyes with a bobbing and weaving string arrangement by the evening’s composer, Andy Thompson. By the second song, “Matches to Paper Dolls,” the entire orchestra had joined in and you could feel the room constricting; everyone seemed to be leaning in, wondering how all these pieces were fitting together to create an almost impressionistic cloud of sound. Dessa still seemed like she was walking on a tightrope, eyeing her longtime touring vocalist Aby Wolf at every opportunity to center herself, and the song ended with the two of them center stage, holding hands like paper dolls, keeping a grip on one another as the show started to ascend.

It wasn’t until after the third song, a dreamy reimagining of her latest single, “Quinine,” that Dessa finally spoke: “I was going to talk for a minute here and say thank you for coming, but I’m too nervous,” she said. “Let’s do this.”

I’m not saying that Dessa wasn’t nervous, but after that ice-breaking there was no way you could have possibly known. A few songs later she was not only chatting warmly with the audience but also dropping f-bombs and sipping from a plastic cup of whiskey, bringing a little bit of the dive bar into Orchestra Hall. After a moving performance of “The Chaconne” that showed off Dessa’s increasingly warm and expressive singing voice, she finally took a moment to banter with the crowd.

“I’m not sure how it is from where you’re sitting, but from where I am it’s clear that both the season ticket holders and the Doomtree fans are here tonight. Thank you to all two of those groups for coming,” she said to wild laughter. She wondered if the classical music fans might go home thinking that all rap music is as sad as hers, joking that she specialized in “romantic devastation — that’s my niche. I could practically give a TED Talk about it.”

With that, stage hands appeared to affix a TED-style headset, raise up a projection screen from the center of the stage, and bring out a clicker for her to use to advance slides while the orchestra played the chords of the TED Talk theme. The crowd lost it. It turns out even Orchestra Hall has a sense of humor.

On paper, offering a TED Talk monologue in the middle of a hip-hop concerto may sound like a gimmick, but in real life it worked. This was her chance to break down every wall that still remained between orchestra and audience and offer up her evening’s mission statement: She finally realized, perhaps in the process of deconstructing her songs for this show, that much of her art has been centered around the fact that she was still in love with an ex-boyfriend who had long since broken her heart. What would her music sound like if she could finally find a way to move on?

So she did what any desperate woman must do: She consulted a team of neuroscientists at the Center for Magnetic Resonance Research at the University of Minnesota who had figured out how to map certain impulses in the brain, and after a series of scans was able to determine just which part of her brain was specifically reacting to memories of her ex. “All I had to do,” she said calmly, “was remove it.”

The screen dropped, the headset came off, and we were back to the music. Suddenly, every word Dessa sang and rapped spoke to this problem she was trying to address; “Call Off Your Ghost” became downright chilling. By the close of the first set, “Warsaw,” Dessa had reached a new level of vulnerability and ferocity, showing her full self to her audience for perhaps the first time. With assistance from a quartet of the city’s finest vocalists — Aby Wolf, Ashley DuBose, Cameron Kinghorn, and Matthew Santos — and the thrust of a full orchestra behind her, Dessa’s voice was the most versatile and strongest I’d ever heard it, like it was coming out of a deeper, more guttural place than she’d been able to access before.

The first set had been such a rousing success — most of the dialogue in the lobby contained varying uses of the word “wow” — that the second set felt like sheer candy, the audience fully settled into the immersive experience, and Dessa completely comfortable with her place on stage. The opening song of the second set, “Dixon’s Girl,” featured only Dessa, her longtime bassist Sean McPherson, and the plucky accompaniment of the orchestra’s upright bassists, harking back to her work in the Castor, the Twin era and offering up a few moments of sheer nostalgic joy. Next she started unveiling new music, starting with the sweeping moving-on anthem “The Good Fight” and following with the poetic ode to harmful impulses, “Velodrome,” giving us a glimpse into her newer, slightly more optimistic point of view.

It was in Dessa’s second monologue where this union of neuroscience, orchestral arrangements, and break-up songs really came into clear view. She explained that she went to visit another neuroscientist, one who could use biofeedback to help her train her brain to react in new ways; by the end of her sessions, she had successfully “resequenced” her thought patterns to stop experiencing love for her ex. To celebrate, she created a 3D model of the portion of her brain that had been triggering this undesired love, which resembled a pair of ram’s horns. And to cap off her show, she lowered a gigantic model of that part of her brain from the ceiling, coated in tiny mirrors, and spun it around like a disco ball. “That’s love,” she said, and the audience roared.

It was hilarious, odd, brainy (literally) and deeply moving. In other words, it was pure Dessa.

The final song of the second act was another new one, “Good Grief,” about powering through the loss of a romantic partner and finding solid ground beyond it. It was an upbeat song in a major key, something new and clearly long-desired for Dessa, and her voice shined as the melody of the song rang out. When she returned for an encore performance of the epic “Sound the Bells,” surrounded by all four vocalists striking defiant poses at center stage, the audience had no choice but to rise to our feet and holler like we were in the loudest bar on earth.